[(2-methoxy-5-nitrophenyl)methyl]triphenylphosphonium bromide | 908863-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2-methoxy-5-nitrophenyl)methyl]triphenylphosphonium bromide
• 英文别名: (2-methoxy-5-nitrobenzyl)(triphenyl)phosphonium bromide；(2-methoxy-5-nitrobenzyl)triphenylphosphonium bromide
• CAS: 908863-87-6
• 化学式: Br*C₂₆H₂₃NO₃P
• 分子量: 508.351
• InChiKey: LEDOPOLOQFUXJL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(2-methoxy-5-nitrophenyl)methyl]triphenylphosphonium bromide 在 三溴化硼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 环己烷 为溶剂， 反应 15.25h， 生成 9-hydroxy-4-(2-methoxy-5-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
  参考文献：
  名称：

  4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure−Activity Relationships for Chromophore Modification and Phenyl Ring Substitution

  摘要：

  High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]carbazole- 1,3(2H,6H)-dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2'-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

  DOI：

  10.1021/jm0512591
• 作为产物：
  描述：

  4-硝基苯甲醚 在 硫酸 、 溶剂黄146 、 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 [(2-methoxy-5-nitrophenyl)methyl]triphenylphosphonium bromide
  参考文献：
  名称：

  New Hits as Antagonists of GPR103 Identified by HTS

  摘要：

  Preclinical data indicate that GPR103 receptor and its endogenous neuropeptides QRFP26 and QRFP43 are involved in appetite regulation. A high throughput screening (HTS) for small molecule GPR103 antagonists was performed with the clinical goal to target weight management by modulation of appetite. A high hit rate from the HTS and initial low confirmation with respect to functional versus affinity data challenged us to revise the established screening cascade. To secure high quality data while increasing throughput, the binding assay was optimized on quality to run at single concentration. This strategy enabled evaluation of a larger fraction of chemical clusters and singletons delivering 17 new compound classes for GPR103 antagonism. Representative compounds from three clusters are presented. One of the identified clusters was further investigated, and an initial structure activity relationship study is reported. The most potent compound identified had a pIC(50) of 7.9 with an improved ligand lipophilic efficiency.

  DOI：

  10.1021/ml400519h

文献信息

• Synthesis and characterization of novel conducting homopolymers based on amino β-styryl terthiophene
  作者：Hakim Mehenni、Lê H Dao

  DOI：10.1139/v08-136

  日期：2008.11.1

  Novel ECPs (electronic conducting polymers) based on amino β-styryl-substituted terthiophene (AST) were synthetized by direct electropolymerization. The ECPs were characterized by cyclic voltammetry, square-wave voltammetry, Fourier transform infrared (FTIR) spectroscopy, and X-ray photoelectron spectroscopy (XPS). The poly(amino β-styryl terthiophene) displayed cyclic and square-wave voltammograms with redox peaks that can be assigned to the aminophenyl moiety and the polyterthiophene backbone. The presence of free primary amine groups on the ECP film permitted further biological functionalization (i.e., covalent bonding of various bioreceptors on its surface). The electrochemical performance of Biotin grafted at the AST modified glassy carbon electrode was investigated to detect the Avidin protein in solution by cyclic voltammetry and square-wave voltammetry.Key words: electronic conducting polymer, electrode surface modification, biosensor, β-styryl-substitued terthiophene, functionalization, cyclic, square-wave voltammetry.

  通过直接电聚合法合成了基于氨基 β-苯乙烯基取代噻吩（AST）的新型 ECP（电子导电聚合物）。通过循环伏安法、方波伏安法、傅立叶变换红外光谱法和 X 射线光电子能谱法对 ECP 进行了表征。聚（氨基 β-苯乙烯基噻吩）显示出循环伏安图和方波伏安图，其氧化还原峰可归属于氨基苯基和聚噻吩骨架。ECP 薄膜上存在的游离伯胺基团允许进一步的生物功能化（即在其表面共价键合各种生物受体）。通过循环伏安法和方波伏安法研究了接枝在 AST 改性玻璃碳电极上的生物素的电化学性能，以检测溶液中的 Avidin 蛋白。
• Structure–activity relationship studies on a novel class of antiproliferative agents derived from Lavendustin A. Part I: Ring A modifications
  作者：Peter Nussbaumer、Anthony P. Winiski

  DOI：10.1016/j.bmc.2008.07.039

  日期：2008.8

  to the "colchicine binding site" on tubulin and, thus, inhibits tubulin polymerization in vitro. Moreover, we established structure-activity relationships for the effect of modifications in the 2,5-dimethoxyphenyl moiety ("ring A") of the molecule on in vitro antiproliferative activity.

  有效的抗增殖剂SDZ LAP 977在光化性角化病患者的临床概念验证研究中已显示出功效，先前已证明它可以阻断有丝分裂中的细胞周期。在本研究中，我们进一步探讨了作用方式：SDZ LAP 977与微管蛋白上的“秋水仙碱结合位点”结合，从而在体外抑制微管蛋白的聚合。此外，我们建立了结构-活性关系，以用于修饰分子的2，5-二甲氧基苯基部分（“环A”）对体外抗增殖活性的影响。